NO312021B1 - Tre-preserveringsmidler, konsentrat av slike og anvendelse av disse midler - Google Patents
Tre-preserveringsmidler, konsentrat av slike og anvendelse av disse midler Download PDFInfo
- Publication number
- NO312021B1 NO312021B1 NO19985538A NO985538A NO312021B1 NO 312021 B1 NO312021 B1 NO 312021B1 NO 19985538 A NO19985538 A NO 19985538A NO 985538 A NO985538 A NO 985538A NO 312021 B1 NO312021 B1 NO 312021B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- wood
- alkyl group
- quaternary ammonium
- amino
- Prior art date
Links
- 239000002023 wood Substances 0.000 title claims description 34
- 239000003795 chemical substances by application Substances 0.000 title claims description 20
- 239000012141 concentrate Substances 0.000 title claims description 8
- 239000003755 preservative agent Substances 0.000 title 1
- 238000005470 impregnation Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 10
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 7
- 244000060011 Cocos nucifera Species 0.000 claims description 7
- 239000003139 biocide Substances 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 6
- 230000003115 biocidal effect Effects 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims description 2
- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000001880 copper compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000003752 zinc compounds Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 claims 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 claims 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
- 239000003171 wood protecting agent Substances 0.000 claims 1
- -1 for example Substances 0.000 description 18
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000007654 immersion Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229940001447 lactate Drugs 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000004251 Ammonium lactate Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229940059265 ammonium lactate Drugs 0.000 description 2
- 235000019286 ammonium lactate Nutrition 0.000 description 2
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 229940049953 phenylacetate Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- BPTPEBDKCNQNIV-ALOPSCKCSA-N (2s,6r)-4-[3-(2-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=CC=C(C(C)(C)C)C=1CC(C)CN1C[C@H](C)O[C@H](C)C1 BPTPEBDKCNQNIV-ALOPSCKCSA-N 0.000 description 1
- PTPLXVHPKMTVIW-FPLPWBNLSA-N (Z)-hydroxyimino-oxido-phenylazanium Chemical compound O\N=[N+](/[O-])c1ccccc1 PTPLXVHPKMTVIW-FPLPWBNLSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 229940044120 2-n-octyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 241000411431 Anobium Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- QTDRLOKFLJJHTG-UHFFFAOYSA-N Furmecyclox Chemical compound C1=C(C)OC(C)=C1C(=O)N(OC)C1CCCCC1 QTDRLOKFLJJHTG-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 description 1
- UBKBVPONTPMQQW-UHFFFAOYSA-N azane;2-hydroxyacetic acid Chemical compound [NH4+].OCC([O-])=O UBKBVPONTPMQQW-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LJOZMWRYMKECFF-UHFFFAOYSA-N benodanil Chemical compound IC1=CC=CC=C1C(=O)NC1=CC=CC=C1 LJOZMWRYMKECFF-UHFFFAOYSA-N 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000009933 burial Methods 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- NKCVNYJQLIWBHK-UHFFFAOYSA-N carbonodiperoxoic acid Chemical compound OOC(=O)OO NKCVNYJQLIWBHK-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GICLSALZHXCILJ-UHFFFAOYSA-N ctk5a5089 Chemical compound NCC(O)=O.NCC(O)=O GICLSALZHXCILJ-UHFFFAOYSA-N 0.000 description 1
- QQODLKZGRKWIFG-UHFFFAOYSA-N cyfluthrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- LZSRUJQDHOIAOD-UHFFFAOYSA-M didecyl(dimethyl)azanium;2-hydroxyacetate Chemical compound OCC([O-])=O.CCCCCCCCCC[N+](C)(C)CCCCCCCCCC LZSRUJQDHOIAOD-UHFFFAOYSA-M 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- QJOOIMSFFIUFKX-UHFFFAOYSA-N methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(Cl)Cl)C1(C)C QJOOIMSFFIUFKX-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- GCOOFSOCGFYRML-UHFFFAOYSA-N n-(dimethylsulfamoyl)-n-(fluoromethylsulfanyl)-2-methylaniline Chemical compound CN(C)S(=O)(=O)N(SCF)C1=CC=CC=C1C GCOOFSOCGFYRML-UHFFFAOYSA-N 0.000 description 1
- RYKDCLAXOJASMK-UHFFFAOYSA-N n-(dimethylsulfamoyl)-n-(fluoromethylsulfanyl)aniline Chemical compound CN(C)S(=O)(=O)N(SCF)C1=CC=CC=C1 RYKDCLAXOJASMK-UHFFFAOYSA-N 0.000 description 1
- LDKKGAXZNKDWEU-UHFFFAOYSA-N n-[1-(6-chloropyridin-3-yl)-4-methyl-4,5-dihydroimidazol-2-yl]nitramide Chemical compound [O-][N+](=O)NC1=NC(C)CN1C1=CC=C(Cl)N=C1 LDKKGAXZNKDWEU-UHFFFAOYSA-N 0.000 description 1
- LXCJGJYAOVCKLO-UHFFFAOYSA-N n-cyclohexyl-n-hydroxynitrous amide Chemical compound O=NN(O)C1CCCCC1 LXCJGJYAOVCKLO-UHFFFAOYSA-N 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 230000007903 penetration ability Effects 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- JUEAPPHORMOWPK-UHFFFAOYSA-M tributylstannyl benzoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C1=CC=CC=C1 JUEAPPHORMOWPK-UHFFFAOYSA-M 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
- A01N59/20—Copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/50—Mixtures of different organic impregnating agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/11—Termite treating
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Mattresses And Other Support Structures For Chairs And Beds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH132696 | 1996-05-28 | ||
| PCT/EP1997/002633 WO1997045236A1 (en) | 1996-05-28 | 1997-05-22 | Wood preservatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO985538L NO985538L (no) | 1998-11-27 |
| NO985538D0 NO985538D0 (no) | 1998-11-27 |
| NO312021B1 true NO312021B1 (no) | 2002-03-04 |
Family
ID=4207843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19985538A NO312021B1 (no) | 1996-05-28 | 1998-11-27 | Tre-preserveringsmidler, konsentrat av slike og anvendelse av disse midler |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US6180672B1 (de) |
| EP (1) | EP0906177B1 (de) |
| JP (1) | JP4300589B2 (de) |
| AT (1) | ATE214653T1 (de) |
| AU (1) | AU720055B2 (de) |
| BR (1) | BR9709373A (de) |
| CA (1) | CA2250986C (de) |
| CZ (1) | CZ294222B6 (de) |
| DE (1) | DE69711179T2 (de) |
| DK (1) | DK0906177T3 (de) |
| EA (1) | EA001109B1 (de) |
| EE (1) | EE03556B1 (de) |
| ES (1) | ES2171261T3 (de) |
| NO (1) | NO312021B1 (de) |
| NZ (1) | NZ332671A (de) |
| PL (1) | PL185079B1 (de) |
| PT (1) | PT906177E (de) |
| SI (1) | SI0906177T1 (de) |
| TR (1) | TR199802443T2 (de) |
| UA (1) | UA48228C2 (de) |
| WO (1) | WO1997045236A1 (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA48228C2 (uk) * | 1996-05-28 | 2002-08-15 | Лонца Аг | Консервант для деревини, спосіб обробки лісоматеріалів, концентрат для виготовлення консерванта для деревини |
| US6172117B1 (en) | 1998-02-27 | 2001-01-09 | Akzo Nobel N.V. | Biocidal preservatives |
| DE60029431T2 (de) | 1999-04-08 | 2007-03-15 | Lonza Inc. | Verfahren zur verbesserung des eindringens von holzschutzmitteln in holz |
| EP1185400B1 (de) | 1999-05-24 | 2006-01-18 | Lonza Inc. | Kupfer/aminoxid-holzschutzmittel |
| ATE289902T1 (de) | 1999-05-24 | 2005-03-15 | Lonza Ag | Azol/amin oxid holzschutzmittel und fungizide |
| PT1185401E (pt) | 1999-05-24 | 2006-08-31 | Lonza Ag | Conservantes de madeira de isotiazolona/oxido de amina |
| MY130072A (en) | 1999-05-24 | 2007-05-31 | Lonza Ag | Amine oxide/iodine containing blends for wood preservation |
| US6231651B1 (en) * | 1999-06-18 | 2001-05-15 | Mississippi State University | Enhanced wood preservative composition |
| JP4809514B2 (ja) * | 2000-02-29 | 2011-11-09 | 大日本木材防腐株式会社 | 非塩素系木材防腐剤 |
| BR0111339B1 (pt) | 2000-05-24 | 2012-03-06 | uso de àxido de amina em composiÇço preservativa de madeira e substrato de madeira. | |
| JP5143992B2 (ja) * | 2000-09-20 | 2013-02-13 | ロンザ アーゲー | 消毒剤 |
| WO2003066294A2 (de) * | 2002-02-07 | 2003-08-14 | Lonza Ag | Nichtwässrige holzschutzmittel |
| US7074459B2 (en) * | 2003-05-23 | 2006-07-11 | Stockel Richard F | Method for preserving wood |
| US20050000387A1 (en) * | 2003-07-02 | 2005-01-06 | Ying Wang | Wood preservative with alkaline copper quaternary |
| US20050112393A1 (en) * | 2003-11-20 | 2005-05-26 | Fliermans Carl B. | Antifungal preservative composition for an environmentally friendly process |
| US20070260089A1 (en) * | 2004-03-26 | 2007-11-08 | Albemarle Corporation | Method for the Synthesis of Quaternary Ammonium Compounds and Compositions Thereof |
| US7993756B2 (en) | 2005-05-04 | 2011-08-09 | Viance, Llc | Long-chain quaternary ammonium compounds as wood treatment agents |
| US7917124B2 (en) * | 2005-09-20 | 2011-03-29 | Accenture Global Services Limited | Third party access gateway for telecommunications services |
| US20070167407A1 (en) * | 2005-12-20 | 2007-07-19 | Albemarle Corporation | Quaternary ammonium borate compositions and substrate preservative solutions containing them |
| MY151415A (en) * | 2006-10-25 | 2014-05-30 | Lonza Ag | Controlled foam alkyl quat formulations |
| GB201010439D0 (en) * | 2010-06-21 | 2010-08-04 | Arch Timber Protection Ltd | A method |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH509038A (de) | 1969-02-26 | 1971-01-29 | Ciba Geigy Ag | Verwendung von quaternären Ammoniumverbindungen zum antimikrobiellen Ausrüsten bzw. zum Schützen von Textilien gegen schädliche Mikroorganismen |
| AT320163B (de) | 1973-01-24 | 1975-01-27 | Hurka Wilhelm | Desinfektionstüchlein |
| DE3319509A1 (de) | 1983-05-28 | 1984-11-29 | Hoechst Ag, 6230 Frankfurt | Neue quaternaere ammoniumverbindungen, verfahren zu deren herstellung und deren verwendung als desinfektionsmittel |
| AT381001B (de) | 1983-11-28 | 1986-08-11 | Arcana Chem Pharm | Verfahren zur herstellung klarer waesseriger desinfektionsmittelloesungen |
| JPH0696243B2 (ja) | 1986-09-05 | 1994-11-30 | 花王株式会社 | 木材防腐剤 |
| JPS63201115A (ja) * | 1987-02-17 | 1988-08-19 | Daicel Chem Ind Ltd | 腋臭防止方法 |
| US5076828A (en) | 1988-11-28 | 1991-12-31 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Oxyalkylated quaternary ammonium compounds and plant growth regulating compositions containing said compounds |
| US5362910A (en) | 1991-10-08 | 1994-11-08 | Nicca Chemical Co., Ltd. | Germicidal and fungicidal agent and a germicidal and fungicidal method |
| ZA943999B (en) | 1993-06-09 | 1995-02-03 | Lonza Ag | Quaternary ammonium and waterproofing/preservative compositions |
| JPH0892013A (ja) * | 1994-09-28 | 1996-04-09 | Shinto Paint Co Ltd | 工業用抗菌組成物 |
| UA48228C2 (uk) * | 1996-05-28 | 2002-08-15 | Лонца Аг | Консервант для деревини, спосіб обробки лісоматеріалів, концентрат для виготовлення консерванта для деревини |
-
1997
- 1997-05-22 UA UA98126905A patent/UA48228C2/uk unknown
- 1997-05-22 NZ NZ332671A patent/NZ332671A/xx not_active IP Right Cessation
- 1997-05-22 PT PT97923985T patent/PT906177E/pt unknown
- 1997-05-22 CA CA002250986A patent/CA2250986C/en not_active Expired - Fee Related
- 1997-05-22 AT AT97923985T patent/ATE214653T1/de active
- 1997-05-22 CZ CZ19983871A patent/CZ294222B6/cs not_active IP Right Cessation
- 1997-05-22 TR TR1998/02443T patent/TR199802443T2/xx unknown
- 1997-05-22 EP EP97923985A patent/EP0906177B1/de not_active Expired - Lifetime
- 1997-05-22 SI SI9730292T patent/SI0906177T1/xx unknown
- 1997-05-22 JP JP54156397A patent/JP4300589B2/ja not_active Expired - Fee Related
- 1997-05-22 EE EE9800416A patent/EE03556B1/xx unknown
- 1997-05-22 DE DE69711179T patent/DE69711179T2/de not_active Expired - Lifetime
- 1997-05-22 DK DK97923985T patent/DK0906177T3/da active
- 1997-05-22 US US09/194,603 patent/US6180672B1/en not_active Expired - Lifetime
- 1997-05-22 BR BR9709373-4A patent/BR9709373A/pt not_active IP Right Cessation
- 1997-05-22 WO PCT/EP1997/002633 patent/WO1997045236A1/en active IP Right Grant
- 1997-05-22 ES ES97923985T patent/ES2171261T3/es not_active Expired - Lifetime
- 1997-05-22 PL PL97330295A patent/PL185079B1/pl unknown
- 1997-05-22 EA EA199801036A patent/EA001109B1/ru not_active IP Right Cessation
- 1997-05-22 AU AU29601/97A patent/AU720055B2/en not_active Ceased
-
1998
- 1998-11-27 NO NO19985538A patent/NO312021B1/no not_active IP Right Cessation
-
2000
- 2000-09-06 US US09/656,505 patent/US6362370B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EE9800416A (et) | 1999-06-15 |
| AU720055B2 (en) | 2000-05-25 |
| NZ332671A (en) | 2000-03-27 |
| TR199802443T2 (xx) | 1999-03-22 |
| WO1997045236A1 (en) | 1997-12-04 |
| EA001109B1 (ru) | 2000-10-30 |
| EA199801036A1 (ru) | 1999-06-24 |
| DK0906177T3 (da) | 2002-07-08 |
| ES2171261T3 (es) | 2002-09-01 |
| SI0906177T1 (en) | 2002-06-30 |
| PL330295A1 (en) | 1999-05-10 |
| CZ387198A3 (cs) | 1999-05-12 |
| DE69711179D1 (de) | 2002-04-25 |
| CA2250986C (en) | 2005-12-27 |
| CZ294222B6 (cs) | 2004-10-13 |
| EE03556B1 (et) | 2001-12-17 |
| NO985538L (no) | 1998-11-27 |
| EP0906177B1 (de) | 2002-03-20 |
| PL185079B1 (pl) | 2003-02-28 |
| ATE214653T1 (de) | 2002-04-15 |
| CA2250986A1 (en) | 1997-12-04 |
| US6180672B1 (en) | 2001-01-30 |
| DE69711179T2 (de) | 2002-08-22 |
| US6362370B1 (en) | 2002-03-26 |
| EP0906177A1 (de) | 1999-04-07 |
| PT906177E (pt) | 2002-09-30 |
| AU2960197A (en) | 1998-01-05 |
| BR9709373A (pt) | 2000-05-09 |
| NO985538D0 (no) | 1998-11-27 |
| JP2000510778A (ja) | 2000-08-22 |
| JP4300589B2 (ja) | 2009-07-22 |
| UA48228C2 (uk) | 2002-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |